US7842197B2 - Conductive material, conductive film, and production method thereof - Google Patents

Conductive material, conductive film, and production method thereof Download PDF

Info

Publication number
US7842197B2
US7842197B2 US11/910,571 US91057106A US7842197B2 US 7842197 B2 US7842197 B2 US 7842197B2 US 91057106 A US91057106 A US 91057106A US 7842197 B2 US7842197 B2 US 7842197B2
Authority
US
United States
Prior art keywords
ionic liquid
conjugated polymer
film
conductivity
contact
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related, expires
Application number
US11/910,571
Other languages
English (en)
Other versions
US20090152503A1 (en
Inventor
Takayuki Kitamura
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Fujikura Ltd
Original Assignee
Fujikura Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Fujikura Ltd filed Critical Fujikura Ltd
Assigned to FUJIKURA LTD. reassignment FUJIKURA LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: KITAMURA, TAKAYUKI
Publication of US20090152503A1 publication Critical patent/US20090152503A1/en
Application granted granted Critical
Publication of US7842197B2 publication Critical patent/US7842197B2/en
Adjusted expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/06—Coating with compositions not containing macromolecular substances
    • C08J7/065—Low-molecular-weight organic substances, e.g. absorption of additives in the surface of the article
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/02—Chemical treatment or coating of shaped articles made of macromolecular substances with solvents, e.g. swelling agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/044—Forming conductive coatings; Forming coatings having anti-static properties
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified macromolecular compounds
    • C08L101/12—Compositions of unspecified macromolecular compounds characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
    • H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
    • H01B1/124—Intrinsically conductive polymers
    • H01B1/125—Intrinsically conductive polymers comprising aliphatic main chains, e.g. polyactylenes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2300/00—Characterised by the use of unspecified polymers
    • C08J2300/12—Polymers characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity

Definitions

  • the apparatuses and methods consistent with the present invention relate to a conductive material, a conductive film, and a production method thereof, and in particular, to an enhancement in conductivity of a ⁇ -conjugated polymer.
  • any one of a method of enhancing the carrier density ‘n’ in a material and a method of improving the mobility ⁇ is used in order to enhance the conductivity ( ⁇ ).
  • the ⁇ conjugated polymer has semiconductor-like conductivity and the conductivity is determined by energy levels of the top of the valence band (HOMO: highest occupied molecular orbital) and the bottom of the conduction band (LUMO: lowest unoccupied molecular orbital) determined by a molecular structure of the polymer, a width (a width of a forbidden band) between the HOMO and the LUMO, and the energy level of impurities doped in the forbidden band.
  • HOMO highest occupied molecular orbital
  • LUMO lowest unoccupied molecular orbital
  • the carrier density can be controlled by the doping in a relatively easy manner, the carrier density is generally reversible in the atmosphere. Meanwhile, the mobility changes greatly by the molecular structure, conformation, packing between polymer chains, crystalline properties, and the like, and thus it is difficult to control or enhance the mobility.
  • a method of controlling or enhancing the conductivity there has been conducted a method of changing the polymerization conditions including a monomer in an electrolyte solution, electrolyte concentration, the type or density of a dopant, the polymerization potential, current density, temperature, and the presence or absence of agitation, during synthesis of ⁇ -conjugated polymers performed by electrolyte polymerization.
  • a method of immersing the ⁇ -conjugated polymers in a dopant solution after polymerization for example.
  • ⁇ -conjugated polymers having certain properties are only synthesized as a result of the polymerization conditions and the method is far from being able to control the conductivity.
  • Embodiments of the present embodiment are contrived in view of these circumstances. It is an exemplary object to provide a conductive material having high conductivity acquired from the ⁇ -conjugated polymer. An embodiment of the invention may also provides a method of controlling and enhancing the conductivity of the ⁇ -conjugated polymer in a simple manner.
  • the inventor has found that it is possible to easily control the conductivity of a ⁇ -conjugated polymer by bring the ⁇ -conjugated polymer into contact with an ionic liquid, which is not disclosed in the related art.
  • a conductive material obtained by bringing the ⁇ -conjugated polymer into contact with the ionic liquid.
  • the conductivity of the conductive material may be 10 times or more the conductivity of the ⁇ -conjugated polymer before being brought into contact with the ionic liquid.
  • a conductive film obtained by bringing the ⁇ -conjugated polymer film into contact with the ionic liquid.
  • the sheet resistance of the conductive material may be 0.1 times or less the sheet resistance of the ⁇ -conjugated polymer film before being brought into contact with the ionic liquid.
  • a method of producing the conductive material including the steps of preparing the ⁇ -conjugated polymer and bringing the ⁇ -conjugated polymer into contact with the ionic liquid.
  • a method of producing the conductive film including the steps of preparing the ⁇ -conjugated polymer film and bringing the ⁇ -conjugated polymer film into contact with the ionic liquid.
  • exemplary embodiments it is possible to enhance the conductivity of a ⁇ -conjugated polymer in a very simple manner. It is possible to arbitrarily control the conductivity by means of a very simple parameter such as a processing time or a processing temperature. Exemplary embodiments can contribute to a performance improvement of almost all electronic devices including a photoelectric conversion element, an electroluminescence element, a sensor, a condenser, and the like which employ the ⁇ -conjugated polymer having conductivity.
  • FIG. 1 is a graph showing a temporal change of a film thickness and a sheet resistance according to Example 1 of an exemplary embodiment to the embodiment.
  • a conductive material can be obtained by bringing a ⁇ -conjugated polymer into contact with an ionic liquid.
  • a conductive film refers to a film-like conductive material, and thus the terminology referrers to as a conductive material includes the conductive film.
  • the ⁇ -conjugated polymer represents a polymer having a ⁇ -conjugate system formed by conjugating two or more of ⁇ bonds (that is, multiple bonds).
  • a specific example of the ⁇ -conjugated polymer includes a salt (PEDOT/PSS) of poly (3,4-ethylenedioxy thiophene) (PEDOT) and poly (styrenesulfonic acid) (PSS).
  • the ⁇ -conjugated polymer may include one kind of ⁇ -conjugated polymer or a ⁇ -conjugated polymer compound in which a plurality of kinds of ⁇ -conjugated polymers are compounded.
  • the ionic liquid which is a salt composed of anion and cation refers to a substance exhibiting a property and a state as a liquid at room temperature.
  • Specific examples of the ionic liquid include liquid imidazolium salts such as iodidated 1-hexyl-3-methylimidazolium (HMImI), bis(trifluoromethane sulfonic acid)imide 1-ethyl-3-methylimidazolium (EMImTFSI).
  • a method of bringing the ⁇ -conjugated polymer into contact with the ionic liquid a method of immersing the ⁇ -conjugated polymer in the ionic liquid and a method of applying to or spraying the ionic liquid on the ⁇ -conjugated polymer may be used.
  • Bringing the ⁇ -conjugated polymer into contact with the ionic liquid can be performed in the atmosphere in a simple manner.
  • a condition at the time of bringing the ⁇ -conjugated polymer into contact with the ionic liquid for example, a processing time or a processing temperature, depends on the available ⁇ -conjugated polymer and ionic liquid, but the processing temperature may be room temperature and a heating temperature, for example. It is possible to arbitrarily control the conductivity by changing the processing time or the processing temperature.
  • the form of the ⁇ -conjugated polymer at the time of bringing the ⁇ -conjugated polymer into contact with the ionic liquid is not particularly limited to a film, a fiber, a granule, a powder, and a mass, but it is desirable that the ionic liquid act on the ⁇ -conjugated polymer evenly.
  • the ⁇ -conjugated polymer has the form of the film (that is, the ⁇ -conjugated polymer film)
  • a film formed on a substrate such as glass is supported through the substrate, and thus, handling thereof becomes easy and the ionic liquid is brought evenly into contact with the entire surface of the film.
  • an additive such as iodine may be added to the ionic liquid within the scope of not negating the advantages of the embodiment.
  • the ionic liquid excessively attached to the ⁇ -conjugated polymer may be removed by washing a material after the contact processing with an organic solvent such as ethanol or acetonitrile. It is possible to remove an excessive organic solvent by drying under room temperature conditions or heating temperature conditions after washing with the organic solvent.
  • the conductivity of the ⁇ -conjugated polymer after being brought into contact with the ionic liquid can be enhanced to 10 times or more the conductivity of the ⁇ -conjugated polymer before being brought into contact with the ionic liquid. Accordingly, the material obtained by bringing the ⁇ -conjugated polymer into contact with the ionic liquid potentially has excellent conductivity utilizable in various kinds of electronic materials, optical functional materials, and magnetic functional materials, and thus the material is useful as a conductive material.
  • the sheet resistance of the ⁇ -conjugated polymer film after being brought into contact with the ionic liquid can decrease to 0.1 times or less the sheet resistance of the ⁇ -conjugated polymer film before being brought into contact with the ionic liquid. Accordingly, the film obtained by bringing the ⁇ -conjugated polymer film into contact with the ionic liquid potentially has excellent conductivity utilizable in various kinds of electronic materials, optical functional materials, and magnetic functional materials, and thus the film is useful as a conductive film.
  • the detailed mechanism that provides the advantage of enhancing the conductivity by bringing the ⁇ -conjugated polymer into contact with the ionic liquid is not clear at the time of application of the embodiment, but the ⁇ -conjugated polymer is believed to undergo a chemical change or a physical change by bringing the ⁇ -conjugated polymer into contact with the ionic liquid from the finding that the conductivity is remarkably enhanced as described in Examples to be described later.
  • the ⁇ -conjugated polymer and the ionic liquid may be compounded.
  • the number of carriers of the conductive material is believed to be the same as that of the ⁇ -conjugated polymer.
  • the ⁇ -conjugated polymer may change in volume (change in film thickness) at the time of being brought into contact with the ionic liquid, there is an advantage of remarkably enhancing the mobility of the carrier of the ⁇ -conjugated polymer from the finding that the conductivity is enhanced in comparison with a change in carrier density resulting from the change in volume (when it is assumed that the conductivity does not change).
  • a film thickness (t) was measured by a contact needle-type surface profile measuring system (Dektak 3030, manufactured by Sloan Company).
  • a sheet resistance ( ⁇ s ) was measured by a resistivity meter (Loresta GP, Model MCP-T610, manufactured by Dia Instruments Co., Ltd.) equipped with a PSP-type probe (MCP-TP06P) having 4 terminals and 4 pins on the basis of JIS K 6911.
  • PEDOT/PSS poly(3,4-ethylenedioxy thiophene)
  • PSS poly poly (styrenesulfonic acid)
  • a 10 (10 mm slide glass was coated with filtrate obtained by filtrating water dispersion liquid (produced by Aldrich) of the PEDOT/PSS with a cellulose acetate filter (0.8 (m) by a cast method.
  • a PEDOT/PSS film, as a conductive film, was obtained by drying the obtained coated film at room temperature for 15 minutes or longer and heat-treating it at 85(C for 15 minutes or longer.
  • the PEDOT/PSS film was immersed in the ionic liquid (iodidated 1-hexyl-3-methylimidazolium: HMImI) and was maintained at 85(C while the PEDOT/PSS film was laid on the slide glass. After cooling the PEDOT/PSS film to room temperature, the PEDOT/PSS film after being brought into contact with the ionic liquid was washed with ethanol and dried.
  • HMImI 1-hexyl-3-methylimidazolium
  • the ionic liquid HMImI was placed at a potential level which did not cause oxidation or reduction of the PEDOT/PSSS, and thus the carrier density (n) of the polymer film did not change.
  • FIG. 1 shows a temporal change of the film thickness and the sheet resistance in Example 1.
  • the number of samples was set to 3.
  • a white circle represents a film thickness of each sample
  • a black circle represents an average value of the film thickness
  • a white triangle represents a sheet resistance of each sample
  • a black triangle represents an average value of the sheet resistance.
  • a “time” shown in FIG. 1 and Table 1 represents a time (that is, the processing time) during which the conductive film was immersed in the ionic liquid (HMImI) and was maintained at 85° C.
  • the PEDOT/PSS film had a film thickness of 2.0 ⁇ 0.3 ⁇ m and a sheet resistance of 4 ⁇ 10 4 to 2 ⁇ 10 5 ⁇ /square, whereas 5 hours after immersing in the ionic liquid, the PEDOT/PSS film had a film thickness of 1.3 ⁇ 0.2 ⁇ m and a sheet resistance of about 2.0 ⁇ 0.4 ⁇ 10 2 ⁇ /square. Therefore, the sheet resistance decreased by 2 digits or more. The film thickness and the sheet resistance almost did not change even after a process time of longer than 5 hours. The conductivity increased by about 3 digits as shown in Table 1, and thus the conductivity was remarkably enhanced with the change in the film thickness and the sheet resistance.
  • the immersion processing was performed in the same manner as Example 1 except for setting a processing temperature of processing the PEDOT/PSS film by using the ionic liquid (HMImI) to room temperature and setting an immersion processing time to 6 days, and thus the film thickness and the sheet resistance of the conductive film were measured before and after being brought into contact with the ionic liquid.
  • a film forming method of the PEDOT/PSSS film was the same as that in Example 1.
  • the measurement result (the average value of three samples) of the film thickness, sheet resistance, and conductivity is shown in Table 2.
  • Example 2 the conductivity after immersing the conductive film in the ionic liquid for 6 days was enhanced up to 500 times as shown in Table 2.
  • the immersion processing was performed in the same manner as Example 1 except for setting the processing temperature of processing the PEDOT/PSS film by using the ionic liquid such as the HMImI, bis(trifluoromethane sulfonic acid)imide 1-ethyl-3-methylimidazolium (EMImTFSI), or a 10:1 mixture of the HMImI and the iodine (I 2 ) to the room temperature and setting the immersion processing time to 40 hours, and thus the film thickness and the sheet resistance of the conductive film were measured before and after being brought into contact with the ionic liquid.
  • a film forming method of the PEDOT/PSSS film is the same as that in Example 1.
  • the measurement result (the representative value of one sample) of the film thickness, sheet resistance, and conductivity is shown in Table 3.
  • the sheet resistance decreased greatly. In other words, after the conductive film was immersed in the ionic liquid for 40 hours, the conductivity was enhanced.
  • the PEDOT/PSS film was performed by a spin coat method (2,500 revolutions per minute, 30 seconds). After a glass was spin-coated with the filtrate obtained by filtrating the water dispersion liquid (produced by Aldrich) of the PEDOT/PSS with the cellulose acetate filter (0.8 ⁇ m), the glass spin-coated with the filtrate was dried for 15 minutes or more at room temperature and then, it was heat-treated for 15 minutes or more at 85° C., thereby obtaining the PEDOT/PSS film. The operation was repeated 3 times so as to produce a PEDOT/PSS film having a film thickness of 0.24 ⁇ 0.04 ⁇ m. Moreover, the film thickness obtained by the spin coat method is approximately 1/10 the film thickness obtained by the cast method described in Example 1.
  • the immersion processing was performed in the same manner as Example 1 except for setting the processing temperature of processing the conductive film to the room temperature and setting the immersion processing time to 7 days, and thus the sheet resistance of the conductive film was measured before and after being brought into contact with the ionic liquid.
  • the measurement result (the average value of three samples) of the sheet resistance is shown in Table 4.
  • the sheet resistance decreased greatly.
  • the sheet resistance decreased by one digit, and thus the conductivity was enhanced.
  • the film forming of the PEDOT/PSS film was performed by the spin coat method in the same manner as Example 4.
  • the immersion processing (for 1 week at room temperature) was performed in the same manner as Example 4 except that the immersion processing is performed by using water, acetonitrile (AN), ethylene carbonate (EC), or toluene (Toluene) instead of the ionic liquid described in Example 4, and thus the sheet resistance of the conductive was measured before and after being brought into contact with the ionic liquid.
  • the measurement result (the average value of three samples) of the sheet resistance is shown in Table 5.
  • the sheet resistance did not almost change or the sheet resistance rather increased, whereas the sheet resistance of the conductive film decreased by using the ionic liquid.
  • the PEDOT/PSS film was easily desorbed from the glass, and thus it was difficult to measure the sheet resistance.
  • the film forming of the PEDOT/PSS film was performed by the spin coat method in the same manner as Example 4.
  • the immersion processing (for 5 hours at 85° C.) was performed in the same manner as Example 1 except that the immersion processing was performed by using a dilute solution (a concentration of 0.2 mol/dm 3 ) of the HMImI, EMImTFSI, or acetonitrile (AN) of lithium perchlorate (LiClO 4 ) instead of the ionic liquid described in Example 1, and thus the sheet resistance of the conductive film was measured before and after being brought into contact with the ionic liquid.
  • the measurement result (the average value of three samples) of the sheet resistance is shown in Table 6.
  • the sheet resistance did not almost change, whereas when the conductive film was processed with a pure ionic liquid, the sheet resistance decreased as described in each of the examples.
  • Embodiments of the embodiment may be used for almost all electronic devices including a photoelectric conversion element, an electroluminescence, a sensor, a condenser, and the like.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Manufacturing & Machinery (AREA)
  • Engineering & Computer Science (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Physics & Mathematics (AREA)
  • Materials Engineering (AREA)
  • Treatments Of Macromolecular Shaped Articles (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Non-Insulated Conductors (AREA)
  • Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Conductive Materials (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Laminated Bodies (AREA)
US11/910,571 2005-04-27 2006-04-05 Conductive material, conductive film, and production method thereof Expired - Fee Related US7842197B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
JP2005129511A JP5052760B2 (ja) 2005-04-27 2005-04-27 導電材料の製造方法
JP2005-129511 2005-04-27
PCT/JP2006/307242 WO2006117967A1 (ja) 2005-04-27 2006-04-05 導電材料および導電膜ならびにそれらの製造方法

Publications (2)

Publication Number Publication Date
US20090152503A1 US20090152503A1 (en) 2009-06-18
US7842197B2 true US7842197B2 (en) 2010-11-30

Family

ID=37307773

Family Applications (2)

Application Number Title Priority Date Filing Date
US11/910,571 Expired - Fee Related US7842197B2 (en) 2005-04-27 2006-04-05 Conductive material, conductive film, and production method thereof
US12/860,577 Abandoned US20100317806A1 (en) 2005-04-27 2010-08-20 Conductive material, conductive film, and production method thereof

Family Applications After (1)

Application Number Title Priority Date Filing Date
US12/860,577 Abandoned US20100317806A1 (en) 2005-04-27 2010-08-20 Conductive material, conductive film, and production method thereof

Country Status (8)

Country Link
US (2) US7842197B2 (de)
EP (1) EP1876607A4 (de)
JP (1) JP5052760B2 (de)
KR (1) KR20080009697A (de)
CN (1) CN101164122B (de)
AU (1) AU2006243103B2 (de)
TW (1) TWI328234B (de)
WO (1) WO2006117967A1 (de)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012023989A2 (en) 2010-08-20 2012-02-23 Rhodia Operations Polymer compositions, polymer films, polymer gels, polymer foams, and electronic devices containing such films, gels, and foams
US20150116172A1 (en) * 2009-04-27 2015-04-30 Drexel University Transparent Conformal Polymer Antennas for RFID and Other Wireless Communications Applications
US20180327543A1 (en) * 2016-01-15 2018-11-15 The Board Of Trustees Of The Leland Stanford Junior University Highly stretchable, transparent, and conductive polymer

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4996505B2 (ja) * 2008-02-28 2012-08-08 日本航空電子工業株式会社 導電性組成物ならびにこれを用いて得られる導電膜および半導体
JP5925423B2 (ja) * 2011-03-31 2016-05-25 日本航空電子工業株式会社 電極酸化防止有機デバイスおよびその製造方法
KR101518104B1 (ko) 2011-06-17 2015-05-06 주식회사 엘지화학 경화성 조성물
CN102544636A (zh) * 2012-01-06 2012-07-04 中国科学院过程工程研究所 一种用于锌空气电池的碱性离子液体电解液
WO2015088999A1 (en) * 2013-12-11 2015-06-18 Rhodia Operations Polymer compositions, films, gels, and foams containing sulfonylimide salts, and electronic devices containing such films, gels, and foams
WO2017085796A1 (ja) 2015-11-17 2017-05-26 株式会社アロマビット 匂いセンサおよび匂い測定システム
CN108269644A (zh) * 2017-01-04 2018-07-10 北京赛特超润界面科技有限公司 一种金属纳米线@离子液体凝胶复合柔性透明电极的制备方法
CN111129329A (zh) * 2019-12-26 2020-05-08 Tcl华星光电技术有限公司 发光电化学池及电致发光显示装置
KR102593821B1 (ko) * 2021-05-12 2023-10-26 이화여자대학교 산학협력단 개질된 전도성 고분자를 포함하는 신축성 전극 및 이를 포함하는 센서
CN116693908A (zh) * 2023-07-26 2023-09-05 浙江大学 一种高电导率的pedot:pss薄膜及其制备方法

Citations (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0180082A1 (de) 1984-10-19 1986-05-07 BASF Aktiengesellschaft Verwendung von elektrisch leitfähigen Polymerisaten zur Absorption von Infrarotstrahlung
JPH01296572A (ja) 1988-05-24 1989-11-29 Tosoh Corp 電池
US5840214A (en) * 1996-07-26 1998-11-24 Monsanto Company Method of increasing polyaniline conductivity with ionic surfactants
WO2000002949A1 (en) 1998-07-09 2000-01-20 Forskarpatent I Linköping Ab Polymer gel electrode
JP2003022938A (ja) 2001-04-13 2003-01-24 Sanyo Chem Ind Ltd 電解コンデンサ
JP2003243028A (ja) 2002-02-14 2003-08-29 Central Glass Co Ltd 電気化学ディバイス
WO2003106571A1 (de) 2002-06-14 2003-12-24 Siemens Aktiengesellschaft Material zur herstellung einer leitfähigen organischen funktionsschicht und verwendung dazu
US6808972B2 (en) 1999-12-21 2004-10-26 Plastic Logic Limited Method of processing solution on a substrate
US6828062B2 (en) * 2000-12-23 2004-12-07 Santa Fe Science And Technology, Inc. Long-lived conjugated polymer electrochemical devices incorporating ionic liquids
JP2005051949A (ja) 2003-07-30 2005-02-24 Matsushita Electric Ind Co Ltd アクチュエータ及びそれを用いた関節駆動機構
US6878297B1 (en) 1999-06-09 2005-04-12 Cambridge Display Technology, Limited Method of producing organic light-emissive devices
US6987663B2 (en) * 2003-10-17 2006-01-17 H.C. Starck Gmbh Electrolytic capacitors with a polymeric outer layer
US20060203322A1 (en) * 2005-03-01 2006-09-14 Bijan Radmard Gel polymers containing ionic liquids
US20080139710A1 (en) * 2004-11-01 2008-06-12 Kaneka Corporation Conductive Composition, Conductive Molded Body and Conductive Gel Composition, and Method for Producing the Same
US7438832B2 (en) * 2005-03-29 2008-10-21 Eastman Kodak Company Ionic liquid and electronically conductive polymer mixtures

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4317010A1 (de) * 1993-05-17 1994-11-24 Zipperling Kessler & Co Dispergierbares intrinsisch leitfähiges Polymer und Verfahren zu dessen Herstellung
CN100382212C (zh) * 2001-04-13 2008-04-16 三洋化成工业株式会社 电解电容器

Patent Citations (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0180082A1 (de) 1984-10-19 1986-05-07 BASF Aktiengesellschaft Verwendung von elektrisch leitfähigen Polymerisaten zur Absorption von Infrarotstrahlung
JPH01296572A (ja) 1988-05-24 1989-11-29 Tosoh Corp 電池
US5840214A (en) * 1996-07-26 1998-11-24 Monsanto Company Method of increasing polyaniline conductivity with ionic surfactants
WO2000002949A1 (en) 1998-07-09 2000-01-20 Forskarpatent I Linköping Ab Polymer gel electrode
US6878297B1 (en) 1999-06-09 2005-04-12 Cambridge Display Technology, Limited Method of producing organic light-emissive devices
US6808972B2 (en) 1999-12-21 2004-10-26 Plastic Logic Limited Method of processing solution on a substrate
US6828062B2 (en) * 2000-12-23 2004-12-07 Santa Fe Science And Technology, Inc. Long-lived conjugated polymer electrochemical devices incorporating ionic liquids
JP2003022938A (ja) 2001-04-13 2003-01-24 Sanyo Chem Ind Ltd 電解コンデンサ
JP2003243028A (ja) 2002-02-14 2003-08-29 Central Glass Co Ltd 電気化学ディバイス
WO2003106571A1 (de) 2002-06-14 2003-12-24 Siemens Aktiengesellschaft Material zur herstellung einer leitfähigen organischen funktionsschicht und verwendung dazu
JP2005051949A (ja) 2003-07-30 2005-02-24 Matsushita Electric Ind Co Ltd アクチュエータ及びそれを用いた関節駆動機構
US6987663B2 (en) * 2003-10-17 2006-01-17 H.C. Starck Gmbh Electrolytic capacitors with a polymeric outer layer
US20080139710A1 (en) * 2004-11-01 2008-06-12 Kaneka Corporation Conductive Composition, Conductive Molded Body and Conductive Gel Composition, and Method for Producing the Same
US20060203322A1 (en) * 2005-03-01 2006-09-14 Bijan Radmard Gel polymers containing ionic liquids
US7438832B2 (en) * 2005-03-29 2008-10-21 Eastman Kodak Company Ionic liquid and electronically conductive polymer mixtures

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
Interchim Green Chemistry Ionic Liquids (no Pub data/no pub date) ppF54 and F63. *
Lu et al "Use of Ionic Liquids for pi-Conjugated Polymer Electrochemical Devices", Science, vol. 297 (( Aug. 2002) pp. 983-987. *
Y. Saito, et al., "I-/I3-redox reaction behavior on poly (3,4-ethylenedioxythiophene) counter electrode in dye-sensitized solar cells" J. Photochem. Photobiol.A:Chem., vol. 164, p. 153.
Y. Saito, et al., "I−/I3−redox reaction behavior on poly (3,4-ethylenedioxythiophene) counter electrode in dye-sensitized solar cells" J. Photochem. Photobiol.A:Chem., vol. 164, p. 153.
Y. Shibata, et al., "Quasi-solid dye sensitised solar cells filled with ionic liquid-increase in efficiencies by specific interaction between conductive polymers and gelators" Chem. Commun., 2003, p. 2730-2731.

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20150116172A1 (en) * 2009-04-27 2015-04-30 Drexel University Transparent Conformal Polymer Antennas for RFID and Other Wireless Communications Applications
US9444134B2 (en) * 2009-04-27 2016-09-13 Drexel University Transparent conformal polymer antennas for RFID and other wireless communications applications
WO2012023989A2 (en) 2010-08-20 2012-02-23 Rhodia Operations Polymer compositions, polymer films, polymer gels, polymer foams, and electronic devices containing such films, gels, and foams
US8784690B2 (en) 2010-08-20 2014-07-22 Rhodia Operations Polymer compositions, polymer films, polymer gels, polymer foams, and electronic devices containing such films, gels and foams
US9378859B2 (en) 2010-08-20 2016-06-28 Rhodia Operations Polymer compositions, polymer films, polymer gels, polymer foams, and electronic devices containing such films, gels and foams
US9552903B2 (en) 2010-08-20 2017-01-24 Rhodia Operations Polymer compositions, polymer films, polymer gels, polymer foams, and electronic devices containing such films, gels and foams
US20180327543A1 (en) * 2016-01-15 2018-11-15 The Board Of Trustees Of The Leland Stanford Junior University Highly stretchable, transparent, and conductive polymer
US11499007B2 (en) * 2016-01-15 2022-11-15 The Board Of Trustees Of The Leland Stanford Junior University Highly stretchable, transparent, and conductive polymer

Also Published As

Publication number Publication date
WO2006117967A1 (ja) 2006-11-09
US20100317806A1 (en) 2010-12-16
AU2006243103A1 (en) 2006-11-09
EP1876607A1 (de) 2008-01-09
KR20080009697A (ko) 2008-01-29
TW200707464A (en) 2007-02-16
CN101164122A (zh) 2008-04-16
JP2006306957A (ja) 2006-11-09
US20090152503A1 (en) 2009-06-18
CN101164122B (zh) 2011-10-26
TWI328234B (en) 2010-08-01
EP1876607A4 (de) 2009-07-15
JP5052760B2 (ja) 2012-10-17
AU2006243103B2 (en) 2011-07-07

Similar Documents

Publication Publication Date Title
US20100317806A1 (en) Conductive material, conductive film, and production method thereof
Cutler et al. Alkoxysulfonate-functionalized PEDOT polyelectrolyte multilayer films: electrochromic and hole transport materials
Bagheri et al. Conductive polymer-based microextraction methods: a review
Chayer et al. Highly conducting water-soluble polythiophene derivatives
Zotti et al. Conductive and magnetic properties of 3, 4-dimethoxy-and 3, 4-ethylenedioxy-capped polypyrrole and polythiophene
Zeglio et al. Conjugated polyelectrolyte blends for electrochromic and electrochemical transistor devices
Wang et al. Stimuli-responsive conjugated copolymers having electro-active azulene and bithiophene units in the polymer skeleton: Effect of protonation and p-doping on conducting properties
Alesary et al. A comparative study of the effect of organic dopant ions on the electrochemical and chemical synthesis of the conducting polymers polyaniline, poly (o-toluidine) and poly (o-methoxyaniline)
Wang et al. Poly (thieno [3, 4-b]-1, 4-oxathiane): medium effect on electropolymerization and electrochromic performance
Liao et al. Efficient n-type small-molecule mixed ion-electron conductors and application in hydrogen peroxide sensors
Lu et al. Novel electroactive proton-doped conducting poly (aromatic ethers) with good fluorescence properties via electropolymerization
Gregory et al. Vapor phase infiltration doping of the semiconducting polymer poly (aniline) with TiCl4+ H2O: mechanisms, reaction kinetics, and electrical and optical properties
Kang et al. Aqueous-alcohol-processable high-mobility semiconducting copolymers with engineered oligo (ethylene glycol) side chains
Yamamoto et al. Poly (thiophene-2, 5-diyl) s with a crown ethereal subunit. Preparation, optical properties, and n-doped state stabilized against air
Hazra et al. Organic mixed ion-electron conductivity in polymer hybrid systems
Khademi et al. Synthesis and characterization of poly (thiophene-co-pyrrole) conducting copolymer nanoparticles via chemical oxidative polymerization
Ramamurthy et al. Synthesis and characterization of high molecular weight polyaniline for organic electronic applications
Alishah et al. Improvement of fill factor by the utilization of Zn-doped PEDOT: PSS hole-transport layers for pin planar type of perovskite solar cells
TW202116729A (zh) 摻雜物、及導電性組成物以及其製造方法
Basha et al. [Retracted] Spectroscopic and Electrochemical Properties of (1‐x)[PVA/PVP]: x [MgCl26H2O] Blend Polymer Electrolyte Films
Hua et al. Water-soluble conducting poly (ethylene oxide)-grafted polydiphenylamine synthesis through a “graft onto” process
Srivastava et al. Electrochemical properties and band gap variation of polyaniline due to the presence of ZnO
US20150188054A1 (en) Cellulose-polymer composites for solar cells
Giglioti et al. Electrochemical and electrochromic response of poly (thiophene-3-acetic acid) films
Soganci et al. Poly (dithienylpyrrole)/Keggin type (nBu4N) 3 [PW9O34 (tBuSiOH) 3] hybrid material: Enhanced optical and electrical properties of conjugated polymers via polyoxometalates

Legal Events

Date Code Title Description
AS Assignment

Owner name: FUJIKURA LTD., JAPAN

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:KITAMURA, TAKAYUKI;REEL/FRAME:019916/0101

Effective date: 20070927

FEPP Fee payment procedure

Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

REMI Maintenance fee reminder mailed
LAPS Lapse for failure to pay maintenance fees
STCH Information on status: patent discontinuation

Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362

STCH Information on status: patent discontinuation

Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362

FP Lapsed due to failure to pay maintenance fee

Effective date: 20141130